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Bile acid


DATA No : BBA0132 INFORMANT : Takashi Iida

NAME : 12-Oxo-5b-cholan-24-oic Acid

COMMON NAME:
SYMBOL:
FORMULA: C24H38O3 MOL.WT (average) : 374.557


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:184.5-187degC, (Me ester; mp, 112-113degC)(Ref. 0063)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D: +95deg (C=0.1, MeOH), [a]D: 101deg (C=0.1, MeOH) (Me ester)(Ref. 0001)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmaxcm-1: 1720, 1700(Ref. 0063)

NMR SPECTRA:1H-NMR (CDCl3) d: 18-Me 1.12(s), 19-Me 1.07(s)(Ref. 0063)
Me ester 1H-NMR (CDCl3) d: 18- and 19-Me 1.03(s), COOMe 3.70(s)(Ref. 0005/0063)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 37.5, C-2 21.0, C-3 26.9, C-4 27.4, C-5 43.1, C-6 26.9, C-7 26.2, C-8 35.8, C-9 44.3, C-10 36.2, C-11 38.1, C-12 214.9, C-13 57.5, C-14 58.7, C-15 24.3, C-16 27.4, C-17 46.5, C-18 11.6, C-19 23.6, C-20 35.6, C-21 18.5, C-22 31.3, C-23 30.5, C-24 174.5, C-25 51.2(Ref. 0004/0064)

MASS SPECTRA:Me ester (22eV) m/z: 388(M+), 273, 233 (Base peak)(Ref. 0009/0063)
The spectrum (70eV) was shown as the Me ester derivative(Ref. 0007)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0001]
AUTHOR:Hill, R. A., Kirk, D. N., Makin, H. L. J., and Murphy, G. M. (1991) Chemical Data, Structures and Bibliographies, in Dictionary of Steroids, Chapman & Hall, London.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0004]
AUTHOR:Barnes, S., and Kirk, D. N. (1988) Nuclear Magnetic Resonance Spectroscopy of Bile Acids, in The Bile Acids-Chemistry, Physiology, and Metabolism (Vol. 4: Methods and Applications) (Setchell, K. D. R., Kritchevsky, D., and Nair, P. P. eds), pp65-136, Plenum Press, New York.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0005]
AUTHOR:Iida, T., and Chang, F. C.
TITLE:Proton Nuclear Magnetic Resonance Spectra of Hydroxylated Bile Acid Isomers and Their Oxo Derivatives
JOURNAL:J. Coll. Engin. Nihon Univ. (A)
VOL:24 PAGE : 163 -165 (1983)
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[0007]
AUTHOR:Lawson, A. M., and Setchell, K. D. R. (1988) Mass Spectrometry of Bile Acids, in The Bile Acids-Chemistry, Physiology, and Metabolism (Vol. 4: Methods and Applications) (Setchall, K. D. R., Kritchevsky, D., and Nair, P. P. eds), pp 167-267, Plenum Press, New York.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0009]
AUTHOR:Elliott, W. H. (1972) Bile Acids, in Biochemical Applications of Mass Spectrometry (Waller, G. R. ed), pp291-312, John Wiley & Sons, Inc. New York.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0063]
AUTHOR:Sawaya, T., and Kimura, M.
TITLE:Autoxidation of Cholanic Acid in the Presence of Ferrous Ions.
JOURNAL:Chem. Pharm. Bull.
VOL:31 PAGE : 1207 -1212 (1983)
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[0064]
AUTHOR:Iida, T., Tamura, T., Matsumoto, T., and Chang, F. C.
TITLE:Carbon-13 NMR Spectra of Oxobile Acid Methyl Esters.
JOURNAL:J. Jpn. Oil Chem. Soc. (Yukagaku)
VOL:32 PAGE : 232 -233 (1983)
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